PhenoFluor™: A Deoxyfluorinating Reagent Convenient Enough to Use in the Hood

The functional-group-tolerant, one-step conversion of phenols to aryl fluorides is a highly desirable process. PhenoFluor™, an innovative reagent developed by Ritter and co-workers,1 provides a straightforward method to fluorinate alcohol and phenols without preactivation and regioselectively fluorinate highly functionalized late-stage intermediates. In collaboration with Tobias Ritter, Aldrich Chemistry now offers two convenient formulation of PhenoFluor™ that can be readily used outside of the glovebox.



General Reaction Scheme

PhenoFluor™ is a thermally stable deoxyfluorinating agent that delivers aryl fluorides from phenols in a one-step, high–yield, ipso substitution reaction. The method is operationally simple, regiospecific, scalable, and compatible with a variety of functional groups including amines, aldehydes, and heterocycles. More recently, it was reported that PhenoFluor™ can be used in a Late Stage Functionalization (LSF) strategy by deoxyfluorinating several natural products and drug-like molecules in a highly regioselective fashion.

 

Representative Substrate Scope

 

Materials List

     

PhenoFluor is a trademark of SciFluor Life Sciences, LLC.

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC